S$ 434 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 18-2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Mon, 9 Mar - Mon, 16 Mar
Air India Logo
14:30 - 21:45
ORD
-
SIN
42h 15m
1 stop
Air India Logo
23:00 - 12:30
SIN
-
ORD
50h 30m
2 stops
S$ 909Air India
Mon, 9 Mar - Mon, 16 Mar
Air India Logo
14:30 - 18:55
ORD
-
SIN
39h 25m
1 stop
Air India Logo
23:00 - 12:30
SIN
-
ORD
50h 30m
1 stop
S$ 958Air India
Mon, 9 Mar - Mon, 16 Mar
Air India Logo
14:30 - 18:55
ORD
-
SIN
39h 25m
1 stop
Air India Logo
23:00 - 12:30
SIN
-
ORD
50h 30m
2 stops
S$ 960Air India
Tue, 10 Mar - Tue, 24 Mar
Turkish Airlines Logo
21:20 - 17:35
ORD
-
SIN
31h 15m
1 stop
Turkish Airlines Logo
05:15 - 11:05
SIN
-
ORD
42h 50m
1 stop
S$ 978Turkish Airlines
Tue, 10 Feb - Thu, 19 Feb
Turkish Airlines Logo
20:20 - 17:35
ORD
-
SIN
31h 15m
1 stop
Turkish Airlines Logo
10:15 - 18:25
SIN
-
ORD
46h 10m
1 stop
S$ 989Turkish Airlines
Thu, 26 Feb - Thu, 5 Mar
Turkish Airlines Logo
20:20 - 08:35
ORD
-
SIN
22h 15m
1 stop
Turkish Airlines Logo
10:15 - 10:05
SIN
-
ORD
37h 50m
1 stop
S$ 991Turkish Airlines
Sun, 29 Mar - Tue, 21 Apr
Delta Logo
09:30 - 05:00
MDW
-
SIN
30h 30m
2 stops
Delta Logo
07:30 - 22:28
SIN
-
MDW
27h 58m
2 stops
S$ 1,200Delta
Tue, 17 Mar - Mon, 30 Mar
Delta Logo
09:35 - 05:00
MDW
-
SIN
30h 25m
2 stops
Delta Logo
22:30 - 12:29
SIN
-
MDW
26h 59m
2 stops
S$ 1,388Delta
Wed, 18 Feb - Wed, 25 Feb
Multiple Airlines Logo
09:00 - 13:05
MDW
-
SIN
38h 05m
2 stops
Multiple Airlines Logo
14:25 - 12:05
SIN
-
MDW
35h 40m
2 stops
S$ 1,587Multiple Airlines
Fri, 10 Apr - Sat, 25 Apr
Multiple Airlines Logo
15:05 - 12:35
MDW
-
SIN
32h 30m
2 stops
Multiple Airlines Logo
13:45 - 05:40
SIN
-
MDW
28h 55m
2 stops
S$ 1,591Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is February, when tickets cost S$ 1,034 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of return tickets is S$ 2,426 and S$ 1,806 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonJanuary
Cheapest flightS$ 434
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (70% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9219 reviews
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

My, Syed Zawar Hussein Shirazi frequently flyer membership number was not included on my boarding pass from O’Hare to Istanbul despite my reminder to the attendant at check in. Further she forgot to give me my boarding pass form Istanbul to Lahore and she needs to improve her customer service, please 🙏

Everything about that day was great I was happy with how things went as a first time traveling with the airline thank you for all that you’ve doing by taking us there to our various destinations thanks.

They oversold the tickets by one which was my ticket so I didn’t have a ticket till last second

Not good. I was supposed to be in Mint but got in economy class

Service was slow and checked bag was off last evening when flying business

Turkish Airline canceled our tickets in the very last minute, with our luggage and everything else, all prepared and good to go. It’s clear that they sold the tickets for better money to someone else. Bad, Bad, Bad business!!!

Awful seating. Bad food. Staff only have one bottle of water and no cans.

it was like a banya -so hot... They did provide a great experience with special food. one toilet broke midflight In general it was a peaceful and relaxing flight - for business class it was good.

Chicago to Istanbul was a much better experience than I expected since I’m more accustomed to Qatar Airways business class. The business lounge in the Istanbul airport was amazing - loved the lockers and phone charging stations, and the bathroom was a spa experience in itself. The onward leg from Istanbul to Karachi was utterly disappointing. Terrible plane, and I felt like I was in economy - the seats don’t come near to lying flat and the food was mediocre. What a sad downgrade - it isn’t as though the ticket on that leg was cheaper. So, on that front, there’s no contest with Qatar airways.

Second leg of Turkish Airline with Indigo is disaster for following reason. 1) You have to carry your cabin bags through ladder to boeing 777 because it was parked somewhere in parking lot and was not given a gate to board passengers and this seems to be people traveling to and fro from those flights and is not issue with flight itself. 2) I choose non vegetarian food on Turkish portal way ahead of checkin to entire trip, However the Indigo flight gave me random veg food saying they code veg food code from Turkish. 3) Indigo did not served any alcoholic beverages stating some weird reason which is non nonsensical. 4)Indigo have TV screens in front of you but it displays nothing except "Welcome Onboard" with annoying white black ground in dark flight. This is the most stupidest and annoying part because you are held hostage for 7 hours and only thing you could do is stare back at white screen which does not have entertainment package or even flight tracker. Such a shame.

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.